# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1544958'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"diaqua[N'-(2-hydroxy-3-methoxyphenyl)methylidene-4-methoxybenzohydrazidato] copper(II) nitrate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Cu N3 O9'
_chemical_formula_weight         460.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0729(3)
_cell_length_b                   11.3899(7)
_cell_length_c                   12.9557(8)
_cell_angle_alpha                72.750(5)
_cell_angle_beta                 75.757(5)
_cell_angle_gamma                74.628(5)
_cell_volume                     945.08(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3236
_cell_measurement_theta_min      4.1620
_cell_measurement_theta_max      72.3920
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             474
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    2.153
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_T_min  0.88318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            8036
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.633
_diffrn_reflns_theta_max         72.395
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3713
_reflns_number_gt                3205
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement. 
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²+0.3574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     280
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4235(4) 0.3246(3) 0.7176(2) 0.0407(5) Uani 1 1 d . . . . .
C2 C 0.5163(4) 0.1979(3) 0.7545(2) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.5890(4) 0.1246(3) 0.6758(2) 0.0441(6) Uani 1 1 d . . . . .
C4 C 0.5758(5) 0.1765(3) 0.5668(2) 0.0518(7) Uani 1 1 d . . . . .
H4 H 0.6267 0.1273 0.5163 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4864(5) 0.3023(3) 0.5321(2) 0.0583(8) Uani 1 1 d . . . . .
H5 H 0.4790 0.3374 0.4582 0.070 Uiso 1 1 calc R U . . .
C6 C 0.4094(5) 0.3745(3) 0.6059(2) 0.0523(7) Uani 1 1 d . . . . .
H6 H 0.3467 0.4580 0.5821 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7474(7) -0.0810(4) 0.6495(3) 0.0754(11) Uani 1 1 d . . . . .
H7A H 0.6428 -0.0829 0.6151 0.113 Uiso 1 1 calc R U . . .
H7B H 0.7954 -0.1639 0.6918 0.113 Uiso 1 1 calc R U . . .
H7C H 0.8546 -0.0524 0.5941 0.113 Uiso 1 1 calc R U . . .
C8 C 0.3430(4) 0.4091(2) 0.7886(2) 0.0411(5) Uani 1 1 d . . . . .
H8 H 0.2822 0.4913 0.7586 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3035(4) 0.4203(2) 1.0589(2) 0.0413(5) Uani 1 1 d . . . . .
C10 C 0.2265(4) 0.5018(2) 1.1359(2) 0.0418(5) Uani 1 1 d . . . . .
C11 C 0.1514(4) 0.6307(3) 1.1034(2) 0.0469(6) Uani 1 1 d . . . . .
H11 H 0.1462 0.6686 1.0296 0.056 Uiso 1 1 calc R U . . .
C12 C 0.0846(4) 0.7029(3) 1.1791(3) 0.0509(7) Uani 1 1 d . . . . .
H12 H 0.0370 0.7890 1.1561 0.061 Uiso 1 1 calc R U . . .
C13 C 0.0887(4) 0.6468(3) 1.2893(3) 0.0496(6) Uani 1 1 d . . . . .
C14 C 0.1616(5) 0.5187(3) 1.3227(3) 0.0572(7) Uani 1 1 d . . . . .
H14 H 0.1630 0.4807 1.3968 0.069 Uiso 1 1 calc R U . . .
C15 C 0.2317(5) 0.4474(3) 1.2468(3) 0.0524(7) Uani 1 1 d . . . . .
H15 H 0.2832 0.3618 1.2700 0.063 Uiso 1 1 calc R U . . .
C16 C -0.0562(5) 0.8399(4) 1.3410(4) 0.0701(10) Uani 1 1 d . . . . .
H16A H 0.0375 0.8822 1.2851 0.105 Uiso 1 1 calc R U . . .
H16B H -0.0858 0.8728 1.4047 0.105 Uiso 1 1 calc R U . . .
H16C H -0.1766 0.8531 1.3137 0.105 Uiso 1 1 calc R U . . .
N1 N 0.3513(3) 0.3763(2) 0.89160(18) 0.0394(4) Uani 1 1 d . . . . .
N2 N 0.2727(3) 0.4628(2) 0.95478(19) 0.0424(5) Uani 1 1 d . . . . .
H2 H 0.2092 0.5377 0.9294 0.051 Uiso 1 1 calc R U . . .
O1 O 0.5429(3) 0.14078(18) 0.85608(16) 0.0488(5) Uani 1 1 d . . . . .
O2 O 0.3976(3) 0.30976(18) 1.09005(17) 0.0502(5) Uani 1 1 d . . . . .
O3 O 0.0277(4) 0.7081(2) 1.3700(2) 0.0653(6) Uani 1 1 d . . . . .
O4 O 0.6724(4) 0.0020(2) 0.71964(18) 0.0580(5) Uani 1 1 d . . . . .
O1W O 0.2279(3) 0.1005(2) 1.05949(18) 0.0526(5) Uani 1 1 d D . . . .
H1A H 0.125(4) 0.151(3) 1.082(3) 0.069(12) Uiso 1 1 d D . . . .
H1B H 0.270(5) 0.050(3) 1.1168(17) 0.057(10) Uiso 1 1 d D . . . .
O2W O 0.6780(4) 0.0879(2) 1.0517(2) 0.0621(6) Uani 1 1 d D . . . .
H2A H 0.714(7) 0.089(4) 1.109(2) 0.089(15) Uiso 1 1 d D . . . .
H2B H 0.714(8) 0.0131(19) 1.045(4) 0.102(18) Uiso 1 1 d D . . . .
Cu Cu 0.47411(6) 0.21583(3) 0.97581(3) 0.04493(17) Uani 1 1 d . . . . .
N3 N 0.7943(4) 0.2278(2) 1.2271(2) 0.0538(6) Uani 1 1 d . . . . .
O31 O 0.9054(4) 0.2830(3) 1.1473(2) 0.0799(8) Uani 1 1 d . . . . .
O32 O 0.7864(7) 0.1179(3) 1.2378(3) 0.1066(12) Uani 1 1 d . . . . .
O33 O 0.6878(8) 0.2833(4) 1.2913(3) 0.1273(18) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.407(4) . ?
C1 C2 1.409(4) . ?
C1 C8 1.440(4) . ?
C2 O1 1.319(3) . ?
C2 C3 1.422(4) . ?
C3 O4 1.370(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.391(5) . ?
C5 C6 1.364(5) . ?
C7 O4 1.417(4) . ?
C8 N1 1.286(4) . ?
C9 O2 1.256(3) . ?
C9 N2 1.343(4) . ?
C9 C10 1.471(3) . ?
C10 C15 1.392(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.381(4) . ?
C12 C13 1.385(5) . ?
C13 O3 1.348(4) . ?
C13 C14 1.385(5) . ?
C14 C15 1.375(4) . ?
C16 O3 1.432(5) . ?
N1 N2 1.384(3) . ?
N1 Cu 1.930(2) . ?
O1 Cu 1.8889(18) . ?
O2 Cu 1.9663(19) . ?
O1W Cu 2.318(2) . ?
O2W Cu 1.975(2) . ?
N3 O33 1.187(4) . ?
N3 O32 1.232(4) . ?
N3 O31 1.249(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.8(3) . . ?
C6 C1 C8 116.9(3) . . ?
C2 C1 C8 123.3(2) . . ?
O1 C2 C1 125.7(2) . . ?
O1 C2 C3 116.7(2) . . ?
C1 C2 C3 117.6(2) . . ?
O4 C3 C4 125.3(3) . . ?
O4 C3 C2 113.4(2) . . ?
C4 C3 C2 121.3(3) . . ?
C3 C4 C5 120.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 121.0(3) . . ?
N1 C8 C1 123.1(2) . . ?
O2 C9 N2 119.1(2) . . ?
O2 C9 C10 120.4(2) . . ?
N2 C9 C10 120.4(2) . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C9 118.1(2) . . ?
C11 C10 C9 123.5(3) . . ?
C12 C11 C10 121.0(3) . . ?
C13 C12 C11 119.8(3) . . ?
O3 C13 C12 124.8(3) . . ?
O3 C13 C14 115.5(3) . . ?
C12 C13 C14 119.7(3) . . ?
C15 C14 C13 120.4(3) . . ?
C14 C15 C10 120.8(3) . . ?
C8 N1 N2 120.0(2) . . ?
C8 N1 Cu 128.12(18) . . ?
N2 N1 Cu 111.85(17) . . ?
C9 N2 N1 114.5(2) . . ?
C2 O1 Cu 126.12(17) . . ?
C9 O2 Cu 113.31(18) . . ?
C13 O3 C16 118.0(3) . . ?
C3 O4 C7 118.6(3) . . ?
O1 Cu N1 93.51(9) . . ?
O1 Cu O2 174.44(8) . . ?
N1 Cu O2 81.10(9) . . ?
O1 Cu O2W 91.61(9) . . ?
N1 Cu O2W 158.41(11) . . ?
O2 Cu O2W 92.93(9) . . ?
O1 Cu O1W 90.75(9) . . ?
N1 Cu O1W 107.75(9) . . ?
O2 Cu O1W 92.20(9) . . ?
O2W Cu O1W 93.13(10) . . ?
O33 N3 O32 119.1(4) . . ?
O33 N3 O31 119.7(3) . . ?
O32 N3 O31 121.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O33 0.93 2.51 3.309(5) 144.3 2_667
N2 H2 O31 0.86 2.03 2.886(3) 171.8 2_667
O1W H1A O31 0.847(10) 2.064(13) 2.903(3) 171(4) 1_455
O1W H1B O1 0.854(10) 2.21(2) 2.847(3) 132(3) 2_657
O1W H1B O4 0.854(10) 2.137(18) 2.936(3) 156(3) 2_657
O2W H2A O32 0.851(10) 1.994(12) 2.839(5) 172(4) .
O2W H2B O1W 0.848(10) 2.04(2) 2.780(3) 146(4) 2_657

_refine_diff_density_max         0.642
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.077



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
